Benzophenone ether esters, processes for their preparation, and their use for improving the light stability of polyester dyeings

ABSTRACT

The present invention relates to compounds of the general formula I ##STR1## in which R 1 , R 2 , R 3 , R 4 , R 5 , x and y are defined as in the description, processes for their preparation, their use for improving the light stability of polyester dyeings and a dyeing process and dye preparations.

The present invention relates to benzophenone ether esters, processesfor their preparation, their use for improving the light stability ofpolyester dyeings and a dyeing process and dye preparations.

A process for improving the light fastness of polyester dyeings, inwhich alkyl ethers of 2,2',4,4'-tetrahydroxybenzophenone are used, hasalready been described in DE-AS 11 56 760. However, this process has anumber of disadvantages. Thus, in the case of bright dyeings, the hue isshifted and the brilliance is reduced to a greater or lesser degree. Thedyes do not show sufficiently good exhaustion onto the fiber, resultingin wastewater problems. Furthermore, the benzophenone derivativesdescribed there have a tendency to migrate during the customary exposureto dry heat setting.

Processes for improving the light fastness of polyester dyeings usingcertain benzophenone ether esters have also already been disclosed inEP-A 254 987 and EP-A 309 909.

Furthermore, benzophenone ether esters which are used for protectingplastics, such as, for example, polyacrylic esters, polymethacrylicesters, polystyrene and ABS polymers, against the effect of UV light aredisclosed in EP 182 056.

The object of the present invention is to provide compounds which leadto an improvement in the light fastness of dyeings on polyestermaterials, without reduction in the exhaustion of the dye onto the fiberand the depth of shade and brilliance of the dyeing.

Surprisingly, this object is achieved by compounds of the generalformula I ##STR2## in which R¹ and R⁴, independently of one another, are(C₁ -C₆)-alkyl, cyano, fluorine, chlorine, bromine, trifluoromethyl orhydrogen;

R² and R³, independently of one another, are (C₁ -C₆)-alkyl or hydrogen;

x and y, independently of one another, are 0, 1 or 2 and

R⁵ represents (C₁ -C₁₂)-alkyl; (C₃ -C₈)-cycloalkyl; (C₁ -C₁₂)-alkyl or(C₃ -C₈)-cycloalkyl, each of which is substituted by (C₁ -C₆)-alkoxy,(C₂ -C₇)-alkoxycarbonyl, amino, (C₁ -C₆)-alkylamino, di-(C₁-C₆)-alkylamino, hydroxyl, cyano, fluorine, chlorine, bromine,trifluoromethyl or nitro; phenyl or phenyl substituted by (C₁-C₆)-alkyl, (C₁ -C₆)-alkoxy, (C₂ -C₇)-alkoxycarbonyl, amino, (C₁-C₆)-alkylamino, di-(C₁ -C₆)-alkylamino, hydroxyl, cyano, fluorine,chlorine, bromine, trifluoromethyl or nitro.

The alkyl, alkoxy, alkoxycarbonyl, alkylamino and dialkylamino radicalscan be straight-chain or branched.

The radicals R¹ and R⁴ can be in the ortho, meta or para positionrelative to the carbonyl group. Where x or y is 2, the substituents canbe in the 1,2-, 1,3- or 1,4-position relative to one another.

The radicals R² and R³ can be bound to all three free positions of thesix-membered ring.

Preference is given to compounds of the general formula I in which

R¹ and R⁴, independently of one another, are hydrogen, (C₁ -C₃)-alkyl,cyano, chlorine or trifluoromethyl,

R² and R³, independently of one another, are hydrogen or (C₁ -C₃)-alkyl,

x and y, independently of one another, are 0 or 1 and

R⁵ is (C₁ -C₄)-alkyl; cyclopentyl, cyclohexyl; (C₁ -C₄)-alkyl,cyclopentyl or cyclohexyl, each of which is substituted by (C₁-C₄)-alkoxy, (C₂ -C₅)-alkoxycarbonyl, amino, (C₁ -C₄)-alkylamino, di-(C₁-C₄)-alkylamino, hydroxyl, cyano, fluorine, chlorine, bromine,trifluoromethyl or nitro; phenyl or phenyl which is substituted by (C₁-C₄)-alkyl, (C₁ -C₄)-alkoxy, (C₂ -C₅)-alkoxycarbonyl, amino, (C₁-C₁₄)-alkylamino, di-(C₁ -C₄)-alkylamino, hydroxyl, cyano, fluorine,chlorine, bromine, trifluoromethyl or nitro.

Particular preference is given to compounds of the general formula I inwhich

R¹, R², R³ and R⁴ are hydrogen,

x and y are 0 and

R⁵ is methyl or phenyl.

The compounds according to the invention of the general formula I can beprepared by reacting a compound of the general formula II ##STR3## inwhich R¹, R², R³, R⁴, x and y are as defined above, with a compound ofthe general formula III ##STR4## in which X represents hydroxyl,halogen, (C₁ -C₄)-alkoxy or --OCOR⁵ and R⁵ is as defined above.

The reaction is advantageously carried out at temperatures of 0° to 150°C., particularly preferably at 50° to 120° C.

Preferably, the reaction is carried out in an inert organic solvent.Suitable solvents of this type are in particular aromatic hydrocarbonshaving 6 to 8 carbon atoms, which may be substituted by a halogen atom,for example by a chlorine atom, or aliphatic halohydrocarbons, forexample chlorohydrocarbons having 1 to 2 carbon atoms. Particularlypreferred solvents are benzene, toluene, xylene, chlorobenzene,chloroform, tetrachloromethane and 1,2-dichloroethane.

The solvent is preferably used in amounts of 1 to 10 liters,particularly preferably 5 to 8 liters, per mole of the compound of thegeneral formula I.

It is particularly advantageous to carry out the reaction in thepresence of an acid catalyst, an inorganic or organic acid beingparticularly suitable. Organic sulfonic acids, such as, for example,p-toluenesulfonic acid, are preferred. Organic sulfonic acids containinghalogen atoms, in particular fluorine atoms, such as, for example,trifluoromethanesulfonic acid, are par-ticularly preferred. Acid ionexchangers are also suitable as acid catalysts.

The catalyst is preferably used in an amount of 1 to 10, particularlypreferably 3 to 6, percent by weight, relative to the compound of thegeneral formula II.

The compound of the general formula III is preferably used in an excessof up to 10 mol per mole of compound of the general formula II. Anexcess of 3 to 8 mol is particularly preferred.

The compounds of the general formula III are carboxylic acids orcarboxylic acid derivatives which are commercially available and/orpreparable by methods known to one skilled in the art. Examples ofcarboxylic acids of this type are aliphatic carboxylic acids, such asacetic acid, propionic acid or butyric acid and aromatic carboxylicacids, such as benzoic acid.

Likewise, the compounds of the general formula I are known from theliterature (see, for example CA 86(1977) 106170 t).

The compounds according to the invention are highly suitable forimproving the light fastness of polyester dyeings. Surprisingly, it hasnow been found that the compounds of the general formula I which havealready been disclosed in EP 182 056 and are preparable by the processesdescribed there, in which R⁵ is a group of the general formula A##STR5## in which

R⁶ is hydrogen, phenyl, (C₁ -C₁₂)-alkyl or cyano and R⁷ and R⁸,independently of one another, are hydrogen, (C₁ -C₈)-alkyl, phenyl orphenyl substituted by (C₁ -C₄)-alkyl or (C₁ -C₄)-alkoxy or together forman alkylene radical having 4 or 5 carbon atoms, are highly suitable forthis purpose.

Accordingly, the present invention also relates to the use of a compoundof the general formula I ##STR6## in which R¹ and R⁴, independently ofone another, are (C₁ -C₆)-alkyl, cyano, fluorine, chlorine, bromine,trifluoromethyl or hydrogen;

R² and R³, independently of one another, are (C₁ -C₆)-alkyl or hydrogen;

x and y, independently of one another, are 0, 1 or 2 and

R⁵ represents (C₁ -C₁₂)-alkyl; (C₃ -C₈)-cycloalkyl; (C₁ -C₁₂)-alkyl or(C₃ -C₈)-cycloalkyl, each of which is substituted by (C₁ -C₆)-alkoxy,(C₂ -C₇)-alkoxycarbonyl, amino, (C₁ -C₆)-alkylamino, di-(C₁-C₆)-alkylamino, hydroxyl, cyano, fluorine, chlorine, bromine,trifluoromethyl or nitro; phenyl or phenyl substituted by (C₁-C₆)-alkyl, (C₁ -C₆)-alkoxy, (C₂ -C₇)-alkoxycarbonyl, amino, (C₁-C₆)-alkylamino, di-(C₁ -C₆)-alkylamino, hydroxyl, cyano, fluorine,chlorine, bromine, trifluoromethyl or nitro, or a group of the generalformula A ##STR7## in which R⁶ is hydrogen, phenyl, (C₁ -C₁₂)-alkyl orcyano and R⁷ and R⁸, independently of one another, are hydrogen, (C₁-C₈)-alkyl, phenyl or phenyl substituted by (C₁ -C₄)-alkyl or (C₁-C₄)-alkoxy or together form an alkylene radical having 4 or 5 carbonatoms, for improving the light fastness of polyester dyeings.

It is particularly advantageous if the compounds of the general formulaI are already used during dyeing, i.e. are present in the dye bath.Accordingly, the present invention also relates to a process for thedyeing of textile polyester material using disperse dyes, characterizedin that the dye bath contains, for improving the light fastness of thedyeing, at least one compound of the general formula I, not only thecompounds according to the invention of the general formula I but alsothe compounds of the general formula I disclosed in EP 182 056, in whichR⁵ represents the group A, being included.

Textile polyester material is understood to mean in particularstructures such as, for example, fibers, yarns, woven fabrics, knittedfabrics and films made of, for example, polyethylene terephthalates,polybutylene terephthalates or polyethylene glycol terephthalates. Thedisperse dyes used are preferably commercially available disperse dyes,such as, for example, azo, anthroquinone, methine, quinophthalone orcoumarin dyes.

Dyeing can take place, for example, by the so-called exhaust methodunder HT conditions, at the boiling temperature with the addition ofcarrier or even by the so-called thermosol method. The dyeing processesmentioned are known to one skilled in the art and described in therelevant literature.

The dye baths contain the compounds of the general formula I in amountsof preferably 0.1 to 10, particularly preferably 0.3 to 5, percent byweight, relative to the textile material to be dyed.

The compounds of the general formula I can be added to the dye baths,for example, as powders, spray-dried/redispersible, or as liquidpreparation in the form of a dispersion.

However, particularly preferably, the compounds of the general formula Iare already present in the dye preparations from which the dye baths areproduced.

Accordingly, the present invention also relates to a dye preparationcharacterized in that it contains at least one compound of the generalformula I, not only the compounds according to the invention of thegeneral formula I but also the compounds of the general formula Idisclosed in EP 182 056, in which R⁵ represents the group A, beingincluded.

The dye preparations according to the invention are liquid orpulverulent disperse dye preparations containing the compounds of thegeneral formula I preferably in amounts of 1 to 50 percent by weight,particularly preferably 1 to 30 percent by weight. The dye content ispreferably 15-40 percent by weight, particularly preferably 20-30percent by weight.

The dye preparations are prepared by milling the dye in the presence ofone or more compounds of the general formula I, one or more dispersantsor one or more emulsifiers and, if desired, in the presence of furtherauxiliaries together in suitable mills.

Examples of suitable mills are ball or sand mills.

The milling process is carried out at 0° to 100° C., preferably at 20°to 70° C.

If it is desired to prepare a pulverulent dispersion, the millingprocess must be followed by spray-drying.

In the case of liquid preparations, the compounds of the general formulaI can also be added after milling, provided they are thoroughly stirredin. Examples of suitable dispersants are anionic or nonionicdispersants, which may also be used together. Examples of anionicdispersants are condensation products of aromatic sulfonic acids withformaldehyde, in particular condensation products ofalkylnaphthalenesulfonic acids with formaldehyde, condensation productsof substituted or unsubstituted phenol, naphthalene- or naphtholsulfonicacids with formaldehyde and sodium bisulfite, alkali metal salts ofcondensation products with formaldehyde and urea and alkali metal saltsof lignosulfonic acids. Alkyl- or alkylarylsulfonates andalkylarylpolyglycol ether sulfates and in particular neutralized estersof an oxethylated novolak. Examples of nonionic dispersants oremulsifiers are ethylene oxide or propylene oxide together withalkylatable compounds, such as, for example, fatty alcohols, fattyamines, fatty acids, phenols, alkylphenols, arylalkylphenols,arylalkylarylphenols and carboxamides, such as, for example, additionproducts of 5 to 10 ethylene oxide units with C₈ -C₁₀ -alkylphenols.

The dispersants mentioned are present in liquid dye preparations in anamount of 15-40 percent by weight, preferably 20-30 percent by weight,and in pulverulent dye preparations in an amount of 20-45% by weight.

The dye preparations according to the invention can also contain furtherauxiliaries, for example those acting as oxidizing agents, such as, forexample, sodium m-nitrobenzenesulfonate or fungicides, such as, forexample, sodium o-phenolphenolate[sic] and sodium pentachlorophenolate.Dye mixtures which are formulated as powders moreover additionallycontain other auxiliaries, such as, for example, wetting or dedustingagents. The dye preparations contain the auxiliaries mentioned inamounts of 0-5 percent by weight, preferably 0-2 percent by weight.

Dyeings which are obtained by the dyeing process according to theinvention, i.e. in the presence of compounds of the general formula I,do not differ or differ only insignificantly from those obtained withoutaddition of the compounds of the general formula I with respect to theirhue. However, they are distinguished by a substantially higher lightfastness, in particular also hot light fastness. Thus, even the highdemands made on dyeings in the automotive sector (seat covers, parcelshelves, and the like) are met and even exceeded.

EXAMPLE 1 (1,3-bis(4-Benzoyl-3-hydroxyphenoxy)-2-propyl methacrylate a)Synthesis

A solution of 97 g (0.2 mol) of1,3-bis(4-benzoyl-3-hydroxyphenoxy)-2-propanol and 103 g (1.2 mol) ofmethacrylic acid in 1200 ml of toluene were heated, after the additionof 6 g of trifluoromethanesulfonic acid, 0.2 g of hydroquinone and 0.2 gof hydroquinone monomethyl ether, at a temperature of 105° to 110° C.for 3 hours. After cooling to room temperature, the reaction mixture waswashed with 3 l of water. The toluene was then distilled off from thereaction mixture at a pressure of 20 mbar. The remaining oily residuewas dissolved in hot ethanol. Cooling of this solution to roomtemperature gave 86 g (78% of theory) of(1,3-bis(4-benzoyl-3-hydroxy)-2-propyl) methacrylate in the form ofcolorless crystals having a melting point of 138° to 139° C. and apurity of 99% (HPLC). The UV spectrum gave two absorption maxima atwavelengths of 287 nm (absorbance of 0.517; extinction coefficient28570) and 324 nm (absorbance of 0.333; extinction coefficient 18400).

b) Dyeing

A dye bath comprising 1500 parts of water, 0.6 part of a dye mixture of

a) a yellow mixture of 0.08 part of Disperse Yellow 42, 0.08 part ofDisperse Yellow 86, 0.08 part of Disperse Yellow 108,

b) a red mixture of 0.035 part of Disperse Red 91, 0.035 part ofDisperse Red 92, 0.035 part of Disperse Red 279,

c) a blue mixture of 0.091 part of Disperse Blue 77, 0.091 part ofDisperse Blue 56, 0.091 part of Disperse Blue 27,

2 parts of ®Dispersogen A (dispersant from Hoechst AG, Frankfurt, WestGermany) and 1.5 parts of the compound from a) is brought to a pH of4.5-5 with acetic acid.

Starting at 60° C., 100 parts of a polyester yarn are dyed in this dyebath using an HT dyeing apparatus. The temperature is increased to 135°C. over a period of 30 minutes, and dyeing is continued at 135° C. foranother 90 minutes. This gives a light gray dyeing which reachessignificantly better light fastnesses in an exposure in the xenon testunder the conditions according to DIN 75202 than a dyeing withoutaddition of the compound from a).

EXAMPLE 2 (1,3-bis(4-Benzoyl-3-hydroxyphenoxy)-2-propyl acetic acidradicals a) Synthesis

A solution of 484 g (1 mol) of1,3-bis(4-benzoyl-2-hydroxyphenoxy)-2-propanol and 360.3 g (6 mol) ofacetic acid in 2.6 1 of toluene was heated, after addition of 6 g oftrifluoromethanesulfonic acid and 5 g of methanesulfonic acid, to refluxin a water separator for 5 hours until, by separation of the calculatedamount of water--18 g--the reaction is complete. After cooling to roomtemperature, the reaction mixture was washed with 5 l of water. Thetoluene was then distilled off from the reaction mixture at a pressureof about 20 mbar. For purification, the remaining residue was dissolvedin a hot mixture consisting of acetone/ethanol.

Cooling of this solution to 15° C. gave 421 g (80% of theory) of(1,3-bis(4-benzoyl-2-hydroxyphenoxy)-2-propanol) acetate in the form offine colorless crystals and a purity of 99% (HPLC). UV, IR and NMRspectra correspond to the compound mentioned.

b) Dyeing

100 parts of a polyester velour are dyed in a dye bath which isanalogous to that from Example 1b) but contains 1.5 parts of thecompound from Example 2a and a dye mixture of 0.43 part of DisperseYellow 51, 0.46 part of a red mixture as in Example 1b) and 0.17 part ofDisperse Blue 77.

This gives an off-pink dyeing which reaches significantly better lightfastness in exposure under the conditions according to DIN 75202 than adyeing without addition of the compound from Example 2a).

EXAMPLE 3 (1,3-bis(4-Benzoyl-3-hydroxyphenoxy)-2-propyl) benzoate. a)Synthesis

141 g (1 mol) of benzoyl chloride were added to a solution of 200 g(0.41 mol) of 1,3-bis(4-benzoyl-3-hydroxyphenoxy)-2-propanyl[sic] and 80g of pyridine at a temperature of 100° to 105° C. over a period of 3hours. A fine precipitate of pyridine hydrochloride formed in the clearsolution. The reaction was completed at 100°-105° C. for another 3hours. After cooling to room temperature, the reaction mixture waswashed with 2 l of water. The toluene was then distilled off from thereaction mixture at a pressure of about 20 mbar. The remaining residuewas purified by recrystallization.

The product thus obtained has a melting point of 168°-169° C. and apurity of 99% (HPLC). UV, IR and NMR spectra correspond to the compoundmentioned.

b) Dyeing

100 parts of a polyester knitted fabric are dyed in a dye bath analogousto that from Example 1b) but containing 2 parts of the compound fromExample 3a) and a dye mixture of 0.46 part of Disperse Yellow 42, 0.17part of a red mixture as in Example 1b) and 0.17 part of a blue mixtureas in Example 1b).

This gives a beige dyeing which, when exposed according to DIN 75202,reaches a significantly better light fastness than a comparable dyeingwithout addition of the compound from Example 3a).

We claim:
 1. Process for the dyeing of textile polyester material usingdisperse dyes, characterized in that the dye bath contains, forimproving the light fastness of the dyeing, at least one compound of thegeneral formula I ##STR8## in which R¹ and R⁴, independently of oneanother, are (C₁ -C₆) -alkyl, cyano, fluorine, chlorine, bromine,trifluoromethyl or hydrogen;R² and R³, independently of one another, re(C₁ -C₆) -alkyl or hydrogen; x and y, independently of one another, are0, 1 or 2 and R⁵ represents (C_(1-C) ₁₂)-alkyl; (C₃ -C₈)-cycloalkyl; (C₁-C₁₂)-alkyl or (C₁ -C₈)-cycloalkyl, each of which is substituted by (C₁-C₆)-alkoxy, (C₂ -C₇)-alkoxycarbonyl, amino, (C₁ -C₆)-alkylamino, di-(C₁-C₆)-alkylamino, hydroxyl, cyano, fluorine, chlorine, bromine,trifluoromethyl or nitro; phenyl or phenyl substituted by (C₁-C₆)-alkyl, (C₁ -C₆)-alkoxy, (C₂ -C₇)-alkoxycarbonyl, amino, (C₁-C₆)-alkylamino, di-(C₁ -C₆)-alkylamino, hydroxyl, cyano, fluorine,chlorine, bromine, trifluoromethyl or nitro, or a group of the generalformula A ##STR9## in which R⁶ is hydrogen, phenyl, (C₁ -C₁₂)-alkyl orcyano and R⁷ and R⁸, independently of one another, are hydrogen, (C₁-C₈)-alkyl, phenyl or phenyl substituted by (C₁ -C₄)-alkyl or (C₁-C₄)-alkoxy or together form an alkylene radical having 4 or 5 carbonatoms.
 2. Process according to claim 1, characterized in that the dyebath contains the compound of the general formula I in amounts of 0.1 to10 percent by weight, relative to the textile material to be dyed. 3.Process according to claim 2, characterized in that the dye bathcontains the compound of the general formula I in amounts of 0.3 to 5percent by weight, relative to the textile material to be dyed.
 4. Aprocess for dyeing using dispersed dyes comprising using a compound ofthe general formula I ##STR10## in which R¹ and R⁴, independently of oneanother, are (C₁ -C₆)-alkyl, cyano, fluorine, chlorine, bromine,trifluoromethyl or hydrogen;R² and R³, independently of one another, are(C₁ -C₆)-alkyl or hydrogen; x and y, independently of one another, are0, 1 or 2 and R⁵ represents (C₁ -C₁₂)-alkyl; (C₃ -C₈)-cycloalkyl; (C₁-C₁₂)-alkyl or (C₃ -C₈)-cycloalkyl, each of which is substituted by (C₁-C₆)-alkoxy, (C₂ -C₇)-alkoxycarbonyl, amino, (C₁ -C₆)-alkylamino, di-(C₁-C₆)-alkylamino, hydroxyl, cyano, fluorine, chlorine, bromine,trifluoromethyl or nitro; phenyl or phenyl substituted by (C₁-C₆)-alkyl, (C₁ -C₆)-alkoxy, (C₂ -C₇)-alkoxycarbonyl, amino, (C₁-C₆)-alkylamino, di-(C₁ -C₆)-alkylamino, hydroxyl, cyano, fluorine,chlorine, bromine, trifluoromethyl or nitro for improving the lightfastness of polyester dyeings.
 5. A process for dyeing using disperseddyes comprising using a compound of the general formula I ##STR11## inwhich R¹ and R⁴, independently of one another, are (C₁ -C₆)-alkyl,cyano, fluorine, chlorine, bromine, trifluoromethyl or hydrogen;R² andR³, independently of one another, are (C₁ -C₆)-alkyl or hydrogen; x andy, independently of one another, are 0, 1 or 2 and R⁵ represents (C₁-C₁₂ )-alkyl; (C₃ -C₈)-cycloalkyl; (C₁ -C₁₂)-alkyl or (C₃-C₈)-cycloalkyl, each of which is substituted by (C₁ -C₆)-alkoxy, (C₂-C₇)-alkoxycarbonyl, amino, (C₁ -C₆)-alkylamino, di-(C₁ -C₆)-alkylamino,hydroxyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or nitro;phenyl or phenyl substituted by (C₁ 14 C₆)-alkyl, (C₁ -C₆)-alkoxy, (C₂-C₇)-alkoxycarbonyl, amino, (C₁ -C₆)-alkylamino, di-(C₁ -C₆)-alkylamino,hydroxyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or nitro,or a group of the general formula A ##STR12## in which R⁶ is hydrogen,phenyl, (C₁ -C₁₂)-alkyl or cyano and R⁷ and R⁸, independently of oneanother, are hydrogen, (C₁ -C₈)-alkyl, phenyl or phenyl substituted by(C₁ -C₄)-alkyl or (C₁ -C₄)-alkoxy or together form an alkylene radicalhaving 4 to 5 carbon atoms, for improving the light fastness ofpolyester dyeings.
 6. Dispersed dye preparations characterized in thatit contains at least one compound of the general formula I ##STR13## inwhich R¹ and R⁴, independently of one another, are (C₁ -C₆)-alkyl,cyano, fluorine, chlorine, bromine, trifluoromethyl or hydrogen;R² andR³, independently of one another, are (C₁ -C₆)-alkyl or hydrogen; x andy, independently of one another, are 0, 1 or 2 and R⁵ represents (C₁-C₁₂)-alkyl; (C₃ -C₈)-cycloalkyl; (C₁ -C₁₂)-alkyl or (C₃-C₈)-cycloalkyl, each of which is substituted by (C₁ -C₆)-alkoxy, (C₂-C₇)-alkoxycarbonyl, amino, (C₁ -C₆)-alkylamino, di-(C₁ -C₆)-alkylamino,hydroxyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or nitro;phenyl or phenyl substituted by (C₁ -C₆)-alkyl, (C₁ -C₆)-alkoxy, (C₂-C₇)-alkoxycarbonyl, amino, (C₁ -C₆)-alkylamino, di-(C₁ -C₆)-alkylamino,hydroxyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or nitro,or a group of the general formula A ##STR14## in which R⁶ is hydrogen,phenyl, (C.sub. -C₁₂)-alkyl or cyano and R⁷ and R⁸, independently of oneanother, are hydrogen, (C₁ -C₈)-alkyl, phenyl or phenyl substituted by(C₁ -C₄)-alkyl or (C₁ -C₄)-alkoxy or together form an alkylene radicalhaving 4 or 5 carbon atoms.
 7. Dispersed dye preparations according toclaim 6, characterized in that it contains the compounds of the generalformula I in amounts of 1 to 50 percent by weight.
 8. Dye preparationaccording to claim 7, characterized in that it contains the compounds ofthe general formula I in amounts of 1 to 30 percent by weight.